In: Chemistry
How do the experimental rates for the Diels-Alder reactions of cyclopentadiene and the different dienophiles correlate to the energies of the calculated LUMO? REFER TO TABLE BELOW! Please explain in detail.
Diels-Alder dienophiles: |
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Label |
Log (rate) |
E (LUMO) (eV) |
Acrylonitrile |
0.00 |
2.85 |
1,1-dicyanoethene |
4.64 |
1.09 |
Cis-1,2-dicyanoethylene |
1.94 |
1.16 |
Trans-1,2-dicyanoethylene |
1.89 |
1.40 |
Tricyanoethylene |
5.66 |
-0.12 |
Tetracyanoethylene |
7.61 |
-1.24 |